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Related Concept Videos

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Isomerism02:43

Isomerism

Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Two similar dibenzo cyclic ethers with dissimilar conformations.

Dennis H Burns1, F Alex Meece, Curtis E Moore

  • 1Department of Chemistry, Wichita State University, 1845 Fairmount, Wichita, KS 67260-0051, USA. dennis.burns@wichita.edu

Acta Crystallographica. Section C, Crystal Structure Communications
|January 9, 2009
PubMed
Summary

Two novel dibenzo cyclic ether compounds were synthesized as scaffolds for phosphate-anion receptors. One compound adopts a bowl-like conformation, ideal for creating anion-selective binding pockets.

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Published on: June 10, 2021

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Dibenzo cyclic ethers serve as versatile scaffolds in chemical research.
  • Developing selective anion receptors is crucial for various chemical and biological applications.

Purpose of the Study:

  • To synthesize and characterize two dibenzo cyclic ether compounds as potential scaffolds for phosphate-anion receptors.
  • To investigate the conformational properties of these compounds and their suitability for anion binding.

Main Methods:

  • Synthesis of two dibenzo cyclic ether derivatives with varying methylene units.
  • Structural characterization using systematic nomenclature and chemical formulas (C16H14Br2O2 and C18H18Br2O2).
  • Conformational analysis to determine the spatial arrangement of the aromatic rings and ether linkages.

Main Results:

  • Two dibenzo cyclic ether compounds were successfully prepared.
  • The compound with a one-methylene unit ether linkage adopted a chair-like conformation with parallel aromatic rings.
  • The compound with a three-methylene unit ether linkage adopted a bowl-like conformation, suitable for convergent functional group placement.

Conclusions:

  • The bowl-like conformation of the dibenzo cyclic ether with a three-methylene unit linkage is promising for developing anion-selective binding pockets.
  • These compounds represent valuable scaffolds for the design of novel phosphate-anion receptors.